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5-substituted 2,4-thiazolidinediones (thiohydantoins). pseudothiohydantoins, and propseudothiohydantoins for use as antiviral agents

a technology of thiohydantoins and substituted thiohydantoins, which is applied in the field of 5substituted2, 4thiohydantoins, pseudothiohydantoins, propseudothiohydantoins and their metforminate salts, can solve the problem of not being able to cyclize jiva-0043 to the corresponding pseudothiohydantoin compound formula

Active Publication Date: 2020-07-30
JIVA PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The compounds demonstrate significant in vitro antiviral activity against HSV-1 and HSV-2, with EC50 values indicating effective inhibition of viral replication and potential for reduced treatment duration and improved patient acceptance due to clear gel or cream formulations, along with potential for oral and parenteral therapies for incipient shingles infections.

Problems solved by technology

However, it was not possible to cyclize JIVA-0043 to the corresponding pseudothiohydantoin compound of Formula (II) under numerous dehydrating reaction conditions, including use of versatile carbodiimide type of reagents.

Method used

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  • 5-substituted 2,4-thiazolidinediones (thiohydantoins). pseudothiohydantoins, and propseudothiohydantoins for use as antiviral agents
  • 5-substituted 2,4-thiazolidinediones (thiohydantoins). pseudothiohydantoins, and propseudothiohydantoins for use as antiviral agents
  • 5-substituted 2,4-thiazolidinediones (thiohydantoins). pseudothiohydantoins, and propseudothiohydantoins for use as antiviral agents

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0050]2, 4-Thiazolidinedione, MW: 117.13, JIVA-0042, may be purchased from Alfa Aesar Chemicals, 99% pure, as a white powder, mp.121-124° C. Alternatively, it may be synthesized by the procedure of, Ge No Meng et al., Organic Preparations and Procedures International 43(3):312-313, January 2011.

example 2

[0051]Metformin hydrochloride, (1, 1-dimethylbiguanide hydrochloride), MW: 165.62 may be purchased from Sigma-Aldrich Co. or is prepared by the method in Procéde dé préparation de chlorhydrate de diméthylbiguanide. Patent FR 2322860, 1975.

example 3

[0052]Pseudothiohydantoin, MW: 116.14, JIVA-0048, Formula (II) where both R and R1 are H, may be purchased from Sigma-Aldrich Co. 97%; mp 249° C. (decomposition). This compound may also be isolated as an intermediate in Example 1.

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Abstract

The present invention concerns the synthesis and use of formulations of 5-substituted 2, 4-thiazolidinediones, pseudothiohydantoins, and propseudothiohydantoins and 2, 4-thiazolidinediones metforminate salts for topical and systemic treatments of infections caused by Herpes simplex viruses and Varicella zoster viruses.

Description

FIELD OF THE INVENTION[0001]The present invention concerns the formulations of 5-substituted-2,4-thiazolidinediones (thiohydantoins), pseudothiohydantoins, propseudothiohydantoins and their metforminate salts, for topical and systemic treatments of infections caused by viruses such as Herpes simplex viruses (HSV1, HSV2), Varicella zoster virus (VZV), Ebola and adeno viruses and other viruses.BACKGROUND OF THE INVENTION[0002]Herpes simplex is a viral disease from the herpesviridae family caused by both Herpes simplex virus type 1 (HSV-1) and type 2 (HSV-2). Infection with the Herpes virus is categorized into one of several distinct disorders based on the site of infection. Oral herpes, Herpes labialis, the visible symptoms of which are commonly called cold sores or fever blisters, is an infection of the face or mouth. Herpes labialis, usually caused by HSV-1, occurs in approximately 90% of cases and affects 20-45% of the adult US population. There is one US Food and Drug Administrati...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): A61K31/426A61K9/08A61K9/06A61P31/22C07C335/32A61K9/48
CPCA61K31/522A61K31/426A61K9/06C07C335/32A61P31/22A61K9/08A61K9/4825A61K2300/00A61K9/0048A61K9/0014A61K47/38
Inventor GOEL, OM P
Owner JIVA PHARMA